Originally Posted by prathmann

First suggestion is to start your adventure in San Francisco and go south. That'll put the prevailing wind at your back and also give you much better views of the ocean along the way. (Yes, you're only about 20' closer to the coast but it makes the difference between looking down at the surf crashing into the rocks below you at the base of a cliff vs. just seeing the distant ocean horizon from the other side of the road.)

Are you going to be camping or have motel stays? The former is much less expensive and easier to arrange since there are lots of Hike&Bike sites that don't require any reservation and are about $5/person-night. When I do this ride I stay at New Brighton State Beach (Capitola), Veteran's Park (Monterey), Big Sur State Park, San Simeon Beach, Oceano, and Refugio.